Evaluation of Several Routes to Advanced Pregabalin Intermediates: Synthesis and Enantioselective Enzymatic Reduction Using Ene-Reductases

Sébastien Debarge; Paul McDaid; Pat O’Neill; James Frahill; John W. Wong; Donncha Carr; Adam Burrell; Simon Davies; Mike Karmilowicz; Jeremy Steflik

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Organic Process Rese...arrow_drop_down

Organic Process Research & Development

Article . 2014 . Peer-reviewed

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https://dx.doi.org/10.1021/op4...

Article

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Evaluation of Several Routes to Advanced Pregabalin Intermediates: Synthesis and Enantioselective Enzymatic Reduction Using Ene-Reductases

descriptionPublicationkeyboard_double_arrow_right Article 03 Jan 2014 English Publisher:American Chemical Society (ACS)Journal:Organic Process Research & Development, volume 18, pages 109-121 (issn: 1083-6160, eissn: 1520-586X,

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Authors: Sébastien Debarge; Paul McDaid; Pat O’Neill; James Frahill; John W. Wong; Donncha Carr; Adam Burrell; +3 Authors

doi: 10.1021/op4002774

Evaluation of Several Routes to Advanced Pregabalin Intermediates: Synthesis and Enantioselective Enzymatic Reduction Using Ene-Reductases

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Abstract

This publication describes the evaluation of four synthetic routes to the advanced pregabalin (Lyrica) intermediate 7. Asymmetric reduction of (E)-7 with an ene-reductase (OPR1 from Lycopersicon esculentum) gave a saturated cyanoester intermediate 5 with the desired S stereocenter in >99% ee. OPR1 also catalyzed the reduction of (Z)-7 to (S)-5, but with lower conversion and selectivity.

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Pfizer (Ireland)
Ireland
Pfizer (United States)
United States

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